Overall: 4.7/5 Food: 4.5/5 - we went in for the burger special which is only available Tuesdays/Wednesdays through April. The burger was very good - extremely flavorful and despite not being a smashburger it had great texture because they have these crispy potato matchsticks in the burger itself. The sauce was also very flavorful - the bun was extremely fluffy and lightly sweet - almost Hawaiian roll esque. No notes on the burger but the fries could have been crispier - but the sauce they came with was also very yummy. We also got the salad and it was quite nice but requires some effort because they leave some of the lettuce in large chunks - the bacon on the salad is stellar but I think overall it could have used something with more acidity or brightness. I would definitely get the burger again :) Service: 5/5 fantastic - our server was super knowledgeable about the wines and equally helpful to our seasoned wine drinkers and the novices. Ambiance: 5/5 cute, great furnishings - we actually did comment that the chairs in the back dining area where we sat were very cozy. When it's not super busy you can easily select a table so I like this back area better. read more

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While the weekly wine challenge on Mondays was fun, my friend and I were put off by the service we received here. After receiving our wine glasses, we felt like we were being ignored for the near two hours we were at Webster's. I understand being busy especially happy hour, but the fact nobody came to check in on us or asked if we wanted to order additional items created a negative experience for us. Our server managed to come around and ask the table next to us if they needed anything really sealed the deal for us. read more

Highly recommend Webster's Wine Bar for their vast selection of wines. Maybe grab a class or two and an app to share. As far as the food, the burger was recommended to us (slagel farms beef) and we found that all three that were ordered were overcooked and dry. Kind of underwhelming. I'd try another dish, perhaps one of their seasonal dishes! I love the space and location and the service. read more

I was honestly very disappointed by my experience with the owner. I had previously been very fond of this establishment and had always enjoyed coming here. However, after a very uncomfortable and disrespectful encounter with the owner, I no longer feel welcome. The interaction came across as extremely racist and made me feel targeted because of the color of my skin. I believe everyone deserves to be treated with respect, and I cannot support a business where I feel that people of my race are treated differently. Because of this experience, I will not be returning. It is unfortunate because I genuinely liked this place before this encounter. read more

We liked this place for the olives and the cheeses. Cheese was fire. Also, the salami was fine. Drinks were okay. Do not under any circumstance get the chicken liver pâté. Unless you like the taste of grey animal. Idk man, the wine and cheese place across from Dimos on Milwaukee gives you a better bang for your buck. This was pricey and a stressful eat. But the place was cozy, cute in there :D, thats it, that's our review. read more

Webster’s Wine Bar - Chicken liver.... - Wine Bars Near Me - Chicago, Illinois

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Great ambiance, very cozy and intimate. I walked by so many times and I'm glad I finally checked it out. They had a lovely wine selection and knowledgeable staff with great recommendations. I'd love to return. read more

Food, service, ambiance are great. The staff is very friendly and knowledgeable. The menu changes frequently but there will be something for everyone. For wine-o's, they have a good per-glass selection but their bottle selection is truly massive. Cheers! read more

Despite having such a bustling culinary scene that now includes some incredible places to enjoy craft beer and spirits, Chicago is not necessarily know. as a city in which to enjoy great wine. Webster's changes that narrative, showcasing some great glass pours and bottles along with a nice food menu and a truly relaxed vibe. It's all about service, creating an experience. Our bartender was kind and friendly, happy to answer any questions, engage us for a brief conversation, and also when to just kind of leave us to our own conversation. You truly can't go wrong with the wine choices, there's something for everyone, and everything is thoughtfully chosen and detailed on the menu. When you call yourself a wine bar, you better know your stuff, and they clearly do. Interesting French malbecs, Syrahs, etc. If we didn't have dinner reservations down the street at Penumbra, we could have stayed and tried several more. We were pleasantly surprised to be able to have our pick of seats on a lovely Saturday evening. Perhaps it's never completely packed? If so, what a great spot to have in your back pocket for a glass or two of wine and a little snack. I say little snack because if you're a vegetarian the menu is quite limited. We had a very cool mushroom and onion galette with a chevre "ice cream." The galette itself was good, but that chevre was quite an experience, absolutely delicious with rich flavors. Otherwise, however, a vegetarian might struggle a bit to go too deep into the menu for dinner. Obviously they're known for oysters and charcuterie, but I would love to be able to do something more than a few apps or a salad for dinner. Maybe that will be different as they approach these warmer months. Overall, however, Webster's remains a premiere option for some of the best wine, and friendliest service, in the city. read more

Webster’s Wine Bar - a glass of red wine - Wine Bars Near Me - Chicago, Illinois

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I LOVE Webster's I used to frequent this spot all the time when I lived in Logan Square. Some of the best glasses of wine I've ever had have been from here. The service and atmosphere are also really good, gives a cozy vibe. We stopped in for a glass of wine before going out for my bachelorette party and, honestly, I could've just stayed at Webster's all night and been very happy. Very much wish I would have written down the wine of the moment at that time because I'd love to buy a bottle. C'est la vie read more

Everything was incredible. Staff, wine selection, food, vibes. All of it. Had the best night with friends here and look forward to doing it again read more

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Had an amazing time here last night- beautiful restaurant with moody lighting and homey decor. The staff was very personable and knowledgeable on their menu as well as good pairings - half of our party were non-drinkers and they had great options! We really enjoyed the cheese and charcuterie, focaccia, oysters, and the tuna tartare. The chocolate cookie? I will return just for that! read more

Good food, but boy they are liberal with the salt shaker. Even after asking them to half-salt the food it comes out excessively salted. The steak and the burger are excellent. read more

Visited Webster's twice in one day during a recent visit to Chicago. For the first visit, I was attending a tasting of Matic wines. These are wines from Slovenia that took me far from my Cabernet/Zinfandel comfort zone. Webster's hosted the tasting and also provided delicious focaccia bread, a tasty olive and cheese salad and warm eggplant hummus to line our tummies. We found ourselves back at Webster's to close out the night. This time, I enjoyed a cheese board, a local pils and great conversations with the bar staff and patrons. This is a warm, convivial spot to enjoy a good drink, elevated snacks and meet some new people. read more

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Located in the corner in Logan square you have a fantastic date spot or place to come for a relaxing glass of wine. The staff are extremely friendly and the space is intimate but large enough. There is also a small sidewalk patio. There is a nice selection of wines from many areas and the staff can help guide you in your choices. The prices are good and they have a perfectly matched food menu. We decided for a New Zealand wine with a charcuterie board. It was a perfect afternoon. read more

Webster’s Wine Bar - Charcuterie board - Wine Bars Near Me - Chicago, Illinois

Websters Wine Bar in Logan Square is this under the radar excellent wine bar that also serves canapés, finger food and lite fare like salads and charcuterie; and a charcuterie board is what we ordered along with our drinks. Websters is kind of this old school rustic bar. This is exactly the sort of place I feel the most comfortable. Their background music is put on "Low" so everyone can hear everyone. I had a terrific Maplewood Pilsner and the others had a very nice Angelo Negro Rosso which they all loved. When the cheeseboard and the soppressata (salami) came out it looked as beautiful as it tasted. This was a very nice spot to come to after a movie or just a late night snack. I glad I was introduced to this place as I will come back here often. read more

The wine selection at Webster's is excellent, but the food and cocktails are also great as well. I've come here twice by myself. Since they don't typically accept reservations, I don't know if there would be a long wait for a larger group.  I would recommend coming early in the evening if you are pressed for time.  There are several high quality sparking, red, white, and sherry wines on the menu. I've had both wine and one of their cocktails (Websters Fancy Manhattan). This cocktail costs a little more than most of the other cocktails on the menu, but worth trying if you love whiskey based drinks. The liked the addition of pesto to the grilled oysters. Good appetizer option.  The burger is a 10/10. It is topped with sharp cheddar, bacon jam, shoestring potatoes, and a charred scallions aioli. I've never noticed this burger on best burgers in Chicago lists, but it definitely belongs there. I would say that this burger is on a similar level as the ones from Table Donkey and Stick and Owen and Engine.  The Crawfish Monica is a great seafood cajun dish. I learned during my second visit that the head chef has ties to New Orleans. It totally makes sense. The flavors tasted very authentic to flavors I've had during past visits to New Orleans. read more

Webster’s Wine Bar - Crawfish Monica - Wine Bars Near Me - Chicago, Illinois

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Popped in randomly and although it was busy we were seated right away! Everyone is super friendly and the service is quick! We shared a bottle of the cab franc ange which was different than a usual cab franc, this was lighter but tasty! We shared a bunch of apps which were oysters, cheese board, fries, and chilled beets. The chilled beets were absolutely delicious, it was so fresh, sweet and salty, I could eat bowls of it. read more

Webster’s Wine Bar - Cheese board - Wine Bars Near Me - Chicago, Illinois

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Cozy little spot good views of the action outside. Just across the street from the blue line which makes for a nice stop off to or from the city. Menu is a little limited, but the staff can help with recommendations. I was the DD and had multiple NA wines and drinks to choose from. Their outdoor tables are great in the summer. read more

Webster’s Wine Bar - Wine and vermouth - Wine Bars Near Me - Chicago, Illinois

Great local place for an upscale dinner and wine. The burger was good, golden beets are a good small plate to share with the group. Would come again and sit in the window or bar for an evening drink. read more

Webster’s Wine Bar - Wine Bars Near Me - Chicago, Illinois

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Loved this place and its vibe! It is open seating everywhere and was still pretty quiet early on a Friday night. The Lambrusco was delicious! Would skip the chips and truffle dip because it didn't come with much. read more

The wine list is great! The wait staff really knows their stuff and can help you pick a wine you will love. The bites are well done and fit the wine. I wish there were more GF choices and that's the reason for the one star deduction. Great date place! read more

Went in here on a Saturday night and ordered a few drinks. Nothing is more annoying then watching a bartender line up the wine glass to a mark on the bar and filling your glass to that exxxxact amount. I get portion control but going about it like this is tacky. Second the other drink we ordered we asked for as a spritz. The guy said no problem, we asked if he made it with Prosecco and he said yes. The drink was actually decent. We had one drink and decided to go somewhere else after because of the large amount of drunk girls screaming at the bar. When we got the bill we handed over the credit card and just happen to notice that they charged us $15 for the drink instead of the $12 listed on the menu. When we asked about it the guy told us he didn't have Prosecco and used the higher cost champagne to make the spritz and that was $15. Now I don't care about $3, but that's not how you do business. If you don't have something you either tell the customer you don't have it. Or you make it and you eat the difference. You don't say I substituted and charged you more without asking you, even though you were sitting at the bar 2 feet away and you just confirmed you were making it with Prosecco. So congratulations you got an extra $3 from us and because of the way you handled it (annoyed and dismissive) when we asked about it, I won't be back. Penny smart, pound foolish. read more

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We had a really pleasant evening here drinking and snacking on delicious cheeses, breads, olives and frites. Really curated selection of wines and cidre. read more

Best, best, best! Service, food, ambiance! This should be the one and only stop for anyone seeking to learn about wines and food pairings! read more

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Worst service of my life! I would put 0/5 if that were an option. The server was incredibly rude, rushed me to order and treated me as if my presence was a burden. read more

This place is a sleeper hit! I've been living in Logan for several years now and have never been. The staff is super knowledgeable on their wines and really helpful. The atmosphere is super relaxing and they have giant windows that also open. They have quiet a selection on tap of natural wines, which is pretty rare . Would definitely be back to try to the food! read more

Lovely small wine bar at the intersection of several busy streets... which makes the outdoor section an interesting spot to people watch. The snack selection was excellent. Of course I had to order the Crawfish Monica (and then go chat with the chef about where he worked in New Orleans... a now closed restaurant that was only blocks from my house) and a cheese plate. I had a lovely Basque sparkline wine in a can (xarmant txakoli) and it was perfection. Their selection of wines was really interesting. Would definitely stop in again. read more

Webster's has a very calm environment where you can enjoy a friends gathering, family dinner, a date or anything you'd like. Decent list of wines and a pretty stacked bar. Expect the wine to be superior to the cocktails. They do have awesome charcuterie and food too. The service at the main room is pretty nice. The server who runs that section more regularly, she's pretty good with her wine suggestions and she's very welcoming too. At the bar, it's a hit or miss. I'm very happy to have this bar within 2min walk. read more

Monday night wine tasting. We went after by chance. Bartender Katie was great! Great food. Recommend

My friend knows I like wine, she recommended this place and I think I might be visiting more often. First of all, try the olives! I asked if they were imported straight from Italy bc they tasted so fresh, it was as if I was sitting back in Italy eating them... the waiter let us know they get them shipped via fedex straight from Italy. They were amazing. I wish they sold some to go. We also tried the Caprese salad, also amazing-- the cheese was delicious! We had the Cava and it was perfect with our appetizers. Will definitely be visiting again. read more

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The cutest wine bar. I came here for a birthday tasting and Charles was so knowledgeable. We loved all the wines we tasted and the food! read more

Webster’s Wine Bar - Wine Bars Near Me - Chicago, Illinois

This is a good option for a fun casual night. We came here on a weeknight and sat at the bar. The place is really cozy and cute and the bartender was really nice. I chose this place initially because I wanted to try orange wine and they have it, we got 2 glasses each the orange and the first white on the list, both were really really good and the pours were big. I would get both again. For food I got the burger and it was actually so good it was a fancy burger with like bacon jam and sharp cheddar and I liked it. My only complaint was the cheese board was expensive for what it is, I'm sure someone who is into cheese would love it but I'm not (I never claimed to be an objective evaluator) and I wouldn't get it again. I loved the wine at this place but wish there were more food options, however I do have plans to go back already. read more

Webster’s Wine Bar - Cheese Board and Orange Wine - Wine Bars Near Me - Chicago, Illinois

Strangely, for a wine bar they didn't have a really impressive selection of individual glasses of wine. However, they do have one of the best burgers currently in the city. It's one of the dying breed of burgers that will still make patties thick enough to cook to your preferred temperature. That used to be a common thing in Chicago but because of Au Cheval (and, most probably, inflation) most places do double thin patties cooked to crunchy cardboard and topped with American processed cheese food. They all remind me of fancy $20 big macs. If that's not your thing (and it's not mine) then you'll appreciate the smoky juicy goodness of this burger. Medium rare, of course. read more

Go for the wine. The Charcuterie leaves a significant amount to be desired. Both the boards in the image below are in Logan Sqaure and about the same price ($40), but the one that isn't Webster's won't leave you feeling like Oliver Twist scrounging for crumbs. read more

Webster’s Wine Bar - CHARCUTERIE - Wine Bars Near Me - Chicago, Illinois

This place is very cute I like the ambiance inside! A good spot for a date or to meet up with friends for a drink. Wine was well priced too. read more

Webster’s Wine Bar - Wine Bars Near Me - Chicago, Illinois

I went to Webster's Wine Bar in the days of yore when it was Telegraph and was happy to see they kept most of the structure of that restaurant. It's a cozy wine & light eats spot divided into a front and back section. Attentive service but not overbearing. We let our server pick our cheeses for us and they were all so amazing! Smart move on our part. We had a brie, manchego and something that was so silky and smooth but I'm unsure on the type. I couldn't get enough of it! That much I know. You can get each cheese individually or 3 for $20 - so why not!? The cheese plate came with sliced up apple, a mouthwatering fruit filled jam and sliced bread. It was just perfect for us! Everything went together just perfectly and had they added some honey on the plate, I would have been in heaven! It was honestly the best cheese plate I have had in ages. We matched our delicious cheese plate with their bacon wrapped, almond stuffed dates for $7. I've had my share of bacon wrapped dates and the almond inside was an interesting little twist. It was a tasty little accompaniment to our vino. They of course have page after page of wine options which is fabulous! Webster's also has a surprisingly good beer list though. I was happy to find a number of brews I had never tried before. Right on! Webster's is a great spot for my friends and I right within walking distance, making it even better! My best gal friend asked me to be her Maid of Honor last night at Webster's so it shall always hold a special place in my heart! read more

Webster’s Wine Bar - Cheese plate - sooooo amazing! - Wine Bars Near Me - Chicago, Illinois

Webster's Wine Bar is fantastic. Great vibes and delicious food. It's a small menu but the options are excellent. Loved the trout and burger! read more

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Wow. I can't believe I found the best burger I've eaten in years at a wine bar, but here I am. I stumbled in here one day walking my dog once I read they had a $12 burger & glass of wine special on Sundays. I took advantage of their cozy little patio where my server Amber provided both excellent service and conversation! Let's get to the burger. This was the juiciest, pinkest-but-not-too-rarest, greatest tasting burger I've had in Chicago, period. Yes, I've been to Au Cheval. This is Chicago's best secret when it comes to burgers. The bun was huge and warm. The cheese was perfectly melted on both patty and bun. I love the fact I can wash my burger down with an amazing tasting glass of red wine (I wish I was cultured enough to tell you what type I exactly had), all for $12. Of course, if you're a wine lover, this is your paradise with an on-site Somm and 400 bottles to choose from. There's a reason I'll be at Webster's almost every free Sunday evening I can get. read more

Webster’s Wine Bar - Sunday means Burger Night. - Wine Bars Near Me - Chicago, Illinois

An Honest Pour My daughter and her boyfriend took my wife and me to an early Wednesday evening dinner at Webster's. Our experience was phenomenal! It is a lovely place, with lots of great design details, two bars, comfortable tables and chairs. Our wonderful server (my wife whispered, "she's beautiful") was attentive without pressure and made a great wine recommendation (La Ferme Rouge, a full-bodied dry red) and helped us all evening. The food was great! The cassoulet was especially flavorful - a dozen spices, I thought!. We also had the mushroom galette and Webster burger. Everything tasted wonderful and was satisfying and fairly-priced. The highlight for me was the Old Bardstown bourbon, which I had never had before. At most places in Logan Square (and within a radius of five miles), I order a double on the rocks. I usually get about 2 to 2-1/2 ounces, but at least I don't have to order twice. At Webster's I got a glass of bourbon filled up to the brim! (Just like I do for myself :)) I was bowled over! I figured at least 4 ounces, and maybe a little more. I had to thank the server, the bartender, the manager -- anyone who would listen -- and compliment them on an honest pour. We loved Websters and strongly recommend an early weekday evening on a day with crummy weather to really enjoy the entire experience! read more

Hidden Gem!!! My friend wanted to go spend the evening at a wine bar and a quick search showed us this place. This is a nice, homly feeling bar with an amazing staff. They got wines from white, red, sparkling and few sweet wines. read more

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